Theoretical investigation on hydrogen bond interaction between adrenaline and hydrogen sulfide

• Published in: Journal of molecular modeling Vol. 26; no. 12; p. 354
• Main Authors: Mohamed, Amr, Fahim, Asmaa M., Ibrahim, Medhat A.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.12.2020
• Subjects: Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Molecular Medicine; Original Paper; Theoretical and Computational Chemistry; Sulfide; NMR, GIAO, NCI, and RDG; ωB97XD/6-311G++(d,p); Adrenaline; H-bonding; FT-IR; NBO; QTAIM
• ISSN: 1610-2940; 0948-5023
• DOI: 10.1007/s00894-020-04602-2

In this study, we elucidated the formation of hydrogen bond between adrenaline (AD) and hydrogen sulfide utilizing computational studies. Six potential complexes were studied including geometrical parameters, energy, vibrational frequency, topological analysis, natural bond orbital (NBO), quantum theory of atoms in molecules (QTAIM), and NMR analysis. Moreover, these calculations were examined through DFT/ωB97XD/6-311G++(d,p) level. It was found that there are no indication on formation on hydrogen bonding between the two catecholic OHs where the one formed between the amino group and the hydroxyl oxygen atom of adrenaline monomer was broken in AS 1 to form two new interactions namely SH ... N and O 1 H 1 ... S, while it retained in other complexes. Furthermore, the bond became stronger due to cooperativity in AS 3 and AS 6 , for the presence of withdrawing effect of the phenyl ring, the H-bonds formed with the side chain oxygen atom. The adrenaline and H 2 S interaction was experimentally examined via FT-IR spectrometry and thin layer chromatography for confirmation of our theoretical study. Graphical abstract